Boron tribromide → 3-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-(2,2,6,6-tetramethyl-4-piperidinyl)propanamide

HRID 11114Notes

Reaction equation

HRID 11114 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:26]C)[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][CH:33]3[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]3)=[O:31])[C:10]=2[CH:9]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:25])[NH:22][C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([OH:26])[CH:14]=[CH:13][C:12]=3[N:11]([CH2:28][CH2:29][C:30]([NH:32][CH:33]3[CH2:38][C:37]([CH3:40])([CH3:39])[NH:36][C:35]([CH3:42])([CH3:41])[CH2:34]3)=[O:31])[C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 867602093-(4-(2-Chlorophenyl)-9-methoxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-(2,2,6,6-tetramethyl-4-piperidinyl)propanamide

Product 1

HCID 867602103-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)-N-(2,2,6,6-tetramethyl-4-piperidinyl)propanamideYield 47%

Procedure

Demethylation of (124) prepared as described in example 237 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (125) as a yellow powder (47%), mp 293–299° C. (dec). 1H NMR δ [(CD3)2SO] 11.08 (br s, 1H), 9.38 (br s, 1H), 8.72 (br, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.83 (d, J=7.1 Hz, 1H), 7.75 (s, 1H), 7.60–7.44 (m, 5H), 7.14 (dd, J=8.8, 2.4 Hz, 1H), 4.70 (t, J=5.8 Hz, 2H), 3.90 (m, 1H), 2.54 (t, J=5.8 Hz, 2H), 1.45–1.31 (m, 2H), 1.30 (s, 3H), 1.29 (s, 3H), 1.25 (s, 3H), 1.22 (s, 3H), 1.09–9.93 (m, 2H). Found: C, 58.67; H, 5.37; N, 8.41. C32H33ClN4O4.1.25CH2Cl2 requires C, 58.79; H, 5.27; N, 8.25.

Sources & evidence

ORD record
ord-23f0286140094cc399e0b44e036c79d9
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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